Hydrochloric Acid → 2-Cyanomethyl-6-methoxy-1-tetralone

HRID 46510Notes

Reaction equation

HRID 46510 reaction equation
Cl.CN([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[C:7]1=[O:18])C.Cl.[C-:20]#[N:21].[K+]>O>[C:20]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[C:7]1=[O:18])#[N:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 124149802-Dimethylaminomethyl-6-methoxy-1-tetralone hydrochloride

Product 1

HCID 128324072-Cyanomethyl-6-methoxy-1-tetralone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13.5 g of 2-dimethylaminomethyl-6-methoxy-1-tetralone hydrochloride (C. A. 41, 6253 g) are dissolved in 200 ml of water and 4 ml of concentrated hydrochloric acid are added, followed by the concentrated aqueous solution of 6.5 g of potassium cyanide, introduced below the surface of the liquid. The mixture is refluxed for one hour, stirred at room temperature overnight and filtered, to yield the 2-cyanomethyl-6-methoxy-1-tetralone melting at 90°-93°. Similarly prepared are the following nitriles: 2-cyanomethyl-1-tetralone, b.p. 125°-30°/0.005 mm Hg; 2-cyanomethyl-6,7-dimethoxy-1-tetralone, m.p. 116°-118°; 2-cyanomethyl-7-methoxy-1-tetralone, m.p. 80°-84°: 2-cyanomethyl-5-methoxy-1-tetralone, m.p. 91°-94°.

Workup

  1. additionintroduced below the surface of the liquid
  2. temperatureThe mixture is refluxed for one hour
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9ea156c7166844fdbe5c2fa34cb8faf3
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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